Trifluoroacetic acid → (2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate

HRID 70873Notes

Reaction equation

HRID 70873 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([CH3:17])[CH2:6][C@H:7]([NH:9]C(OC(C)(C)C)=O)[CH3:8])[CH3:2].[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([CH3:17])[CH2:6][C@H:7]([NH2:9])[CH3:8])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86648195(2R,4R)-4-tert-butoxycarbonylamino-2-methyl-pentanoic acid ethyl ester

Product 1

HCID 86648194(2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate

Procedure

Next, (2R,4R)-4-tert-butoxycarbonylamino-2-methyl-pentanoic acid ethyl ester (142 mg, 0.548 mmol) is added to trifluoroacetic acid (5 mL). After 10 minutes, the solvent is removed under reduced pressure. Methylene chloride is added and the solvent is removed under reduced pressure to give (2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate. This material is used directly in the subsequent coupling reaction.

Workup

  1. customthe solvent is removed under reduced pressure
  2. additionMethylene chloride is added
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f3b845b8de94483883d124b853de19a1
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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